Information Return Intelligence

Q2 2026 Roundup: W-9 Drafts, Backup Withholding, IRIS Updates & More The second quarter of 2026 brought a surprising number of developments in the information reporting world, and in this episode of Information Return Intelligence, Jason Dinesen breaks down the biggest stories that matter to 1099 professionals. Topics include the latest draft Form W-9 and the IRS's reversal on the propose...

Why did Congress try to lower the Form 1099-K reporting threshold to $600—and why did it eventually reverse course? In Part 2 of our Form 1099-K series (find Part 1 here:  https://youtu.be/NDv7rk0m6Ws), Jason Dinesen examines the reasoning behind the proposed change, the practical problems it created, and why Congress ultimately restored the original reporting thresholds. Topics include: The histo...

Why did Congress try to lower the Form 1099-K reporting threshold to $600—and why did it eventually reverse course? In Part 2 of our Form 1099-K series (find Part 1 here:  https://youtu.be/NDv7rk0m6Ws), Jason Dinesen examines the reasoning behind the proposed change, the practical problems it created, and why Congress ultimately restored the original reporting thresholds. Topics include: The histo...

In Part 2 of our three-part series on Form 1099-K, we move beyond the mechanics of the form and examine one of the biggest controversies in information reporting: the proposal to lower the Form 1099-K reporting threshold to just $600. Find Part 1 here . Why did Congress originally push for the change? What was it hoping to accomplish? And why did lawmakers ultimately reverse course and restore the...

In this episode of Information Return Intelligence, we discuss the recent updates to the 1099 NEC and Miscellaneous forms for 2026. Most of the episode is focused on tips and overtime, and we dive into the implications of these changes, particularly regarding worker classification and the reporting of tips for contractors. 

 Form 1099-K has become one of the most misunderstood information returns in the tax world. Between shifting reporting thresholds, IRS delays, and years of media coverage, many businesses and tax professionals know the form exists—but aren't entirely sure when it applies. In Part 1 of this three-part series, Jason Dinesen breaks down the basics of Form 1099-K, including the difference between...

The Treasury Department has released proposed regulations that would update the backup withholding rules to align with the new information reporting thresholds created by the One Big Beautiful Bill. For decades, the familiar $600 reporting threshold under Sections 6041 and 6041A remained unchanged. Beginning in 2026, that threshold increases to $2,000 and will be adjusted annually for inflation. H...

 The recent Kwong case has generated significant discussion in the tax community, particularly regarding whether taxpayers may be entitled to refunds of certain IRS penalties assessed during the COVID-19 pandemic. In this episode of Information Return Intelligence , Jason Dinesen examines the case from a different perspective: What does Kwong mean for information reporting professionals? Topics in...

In this episode of Information Return Intelligence, Jason breaks down a recent IRS private letter ruling that answers a deceptively simple question: Do tax-exempt organizations still have 1099 reporting obligations? The ruling involved a Native American tribe that awarded prize money at a powwow and questioned whether those payments required Form 1099 reporting. The tribe made three key arguments:...

At this year’s IOFM Spring Conference in Orlando, one theme kept surfacing over and over again: uncertainty. In this episode of Information Return Intelligence , Jason shares his biggest takeaways from conversations with AP professionals, compliance teams, and attendees across the conference floor. While the sessions themselves were valuable, the real insights came from listening to the concerns p...

It's another Ask the Experts feature. The questions addressed this time: --What if you have to re-issue a check to the payee because they lost it, and it's the next year? Do you need to correct anything or issue new 1099s? --Is a collection agency associated with a medical facility providing a "medical service" reportable on 1099-MISC (box 6) --Is a non-cash amount, such as a b...

The IRS has released a new draft of Form W-9—and this one brings welcome relief for accounts payable teams. In this episode, Jason breaks down the May 4 draft update and explains why the IRS’s decision to remove the proposed restriction on sole proprietors using EINs is a big deal. That controversial change would have created a massive compliance burden, forcing companies to re-solicit W-9s and re...

This week on Information Return Intelligence, we break down one of the most overlooked areas of 1099 compliance: electronic delivery to recipients. Most organizations are used to thinking about e-filing with the IRS—but what about actually getting the form to the recipient? If you’re emailing PDFs of 1099s (and let’s be honest, most people are), there’s a good chance you’re not fully compliant wit...

This week on Information Return Intelligence, Jason Dinesen breaks down a developing story from the Treasury Department and IRS that could significantly impact how organizations deliver 1099s—and other information returns—to recipients. The Treasury has issued proposed regulations to simplify electronic delivery (eDelivery) for Form 1099-DA (digital assets), while the IRS is simultaneously request...

 In this recurring feature, we tackle various questions that people have submitted recently about 1099s and 1042-S. This episode: --The draft of a new W-9: can you use it? --Is FIRE really being shut down? What about file formatting in IRIS? --Does the credit card exception apply to Form 1042-S? --What if a vendor checks box 3b on the W-9? 

This episode recaps what happened in the 1099 and 1042-S world in the first quarter of 2026. Highlights: --Still no new W-9, but draft W-9 instructions released --Do Native American tribes need to issue 1099s? --FIRE shutdown becomes clearer --2026 drafts of 1099-NEC and 1099-MISC --Treasury Department seeks comment on providing forms to recipients electronically --And more!

The IRS dropped another round of draft 2026 forms on March 27th — updated versions of the 1099-NEC and 1099-MISC — and we still don't have a final version, which is notably late compared to prior years. Jason walks through what's changed in the latest drafts, including the new boxes for reporting tips and overtime pay, and a cosmetic redesign of the name and address fields that's pr...

The IRS has been signaling for months that the FIRE system — one of its two electronic intake systems for information returns — is on its way out. But earlier 2026 drafts of Publication 1099 left some wiggle room in the language. The March 2026 draft doesn't. Jason Dinesen walks through exactly what the updated publication says, explains what FIRE and IRIS actually are and why the distinction...

A followup to last week's episode, as the IRS did end up releasing an efile waiver procedure for Form 1042. But just because the procedure exists doesn't mean you should use it. To request a waiver, you'll need to demonstrate hardship, document the steps you've already taken to comply, provide a cost computation, outline your plan to e-file in the future, and have an authorized...

Form 1042 is due March 16th, and e-filing it is more complicated than you might expect. Jason Dinesen explains why Form 1042 uses the IRS's MeF system instead of IRIS or FIRE, what the e-file mandate means for your organization, and why filing a Form 7004 extension is likely your best move if you don't have a clear path to electronic filing. Sponsored by IOFM — iofm.com.

March 2026 has several information return deadlines you don't want to miss. Jason Dinesen covers the March 16th due dates for Form 1042-S and Form 1042, explains the e-filing complications with Form 1042 and why an extension (Form 7004) might be the smart play, and flags the March 31st Form 1095-B deadline that catches small businesses off guard. Extension forms 8809 and 15397 are also covere...

Single-member LLCs and Form W-9 continue to cause confusion — especially when it comes to which taxpayer identification number (TIN) should be provided. In this episode of Information Return Intelligence , Jason Dinesen tackles a common (and frustrating) issue: single-member LLCs taxed as disregarded entities providing the LLC’s EIN instead of the owner’s Social Security number (or the owner’s EIN...

You filed your 1099s. Now you found a mistake. What do you do? In this episode of Information Return Intelligence , I break down: ✅ Why we file 1099s in the first place (hint: it’s about IRS matching programs and tax compliance) ✅ How the IRS actually uses the data you submit ✅ What kinds of errors matter (and which ones don’t) ✅ When you are required to file a correction ✅ The key August 1 d...

he January 31 deadline for Form 1099-NEC filing has passed—but that doesn’t mean it’s time to stop thinking about information returns. In this episode of Information Return Intelligence, Jason Dinesen breaks down five practical things organizations should do right now to strengthen their 1099 and information return process for the rest of 2026 and beyond. If you only do one thing, Jason explains w...

In this episode of Information Return Intelligence , I break down the draft 2026 versions of Forms 1099-NEC and 1099-MISC and explain what’s really going on with the new boxes for tips and overtime . These changes are tied to the Big Beautiful Bill and the new above-the-line deduction for qualifying tips and qualifying overtime on individual tax returns. While this feels like a payroll issue (and...